Well, this has been quite an interesting read. I was afraid the introduction of the romance’s elements is going to be quite awkward, but you have done well with Rarity serving as a matchmaker The flow was nice as well, though what distracted me a bit were the not so scarce formatting errors (double spaces between paragraphs, a few lines of various speakers merged together etc.) and also some rambling dialogues. If you have a character speaking, it is good to break their lines by actions more frequently. It also helps signify changes in the background, so that your audience won’t be surprised that the characters talked for what seems like a few minutes, yet it’s suddenly dark outside. Furthermore, watch out for recurring issues with incorrectly used or missing punctuation in direct speech, as well as for some random errors in sentence structure and capitalization.

Anyway, have a like and good luck in your writing!